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For the majority of his life, Chester lived in Highfield. It is known that when Chester was younger, he lost his sister in a car accident. He went to the same school as Will Burrows. Due to them both being outcasts and constantly being bullied by there school students, they became each others first best friend.

During the events of Tunnels, Chester makes his debut appearance, with Will showing him his underground base. They explore the tunnel leading off to a strange brick structure. After Dr. Burrows disappeared, the two friends began an investigation to find his whereabouts. One night they broke into the museum that he worked at, finding clues about his expedition to the Colony.

The next day, Will almost got in a fight with the bully named Speed, but Chester defended Will and helped to stop the fight from happening. This moment symbolized their friendship.

Later that day the duo investigated the cellar at Will's house, where Dr. Burrows spent most of his time. After a futile search, they discovered the tunnel that Dr. Burrows must have gone down. They begin to excavate it over the course of several weeks; during this time, several Colonists attempt to abduct Will and Chester, with the duo barely escaping. After another week, they reach the end of the tunnel, and after packing supplies, head down. Chester is fearful of what lies below, as they come across an old elevator and grotto. They eventually reach the Colony, where Chester is in awe of it, but wants to head back. They are soon arrested and imprisoned in the Hold by the Second Officer. Chester, along with Will, has to be subject to the Styx's Dark Light interrogations. The whole experience makes him sick and weak. Eventually Will learns about his real family underground and leaves to live with them, leaving Chester alone in the Hold. He prays that Will might be able to rescue him.

Later on, during Uncle Tam's escape plan, Will goes to visit Chester in the Hold. After discussing the plan secretly, Will says goodbye to Chester as the Second Officer locks his cell door. However, Will blinds the officer with his camera and knocks him out with his shovel, allowing Chester to escape. The two run off and find the entrance to the Eternal City. As they put on the gas masks and prepare to run, the plan goes awry- Cal and Bartleby appear, followed by the Styx. As Will and Cal try to escape through the thick door to the Eternal City, Chester is tugged into the Styx horde. Despite fighting back, he is captured, and Will is horrified at losing his friend so soon.

Once back in the Hold, Chester is treated even worse than before. The Second Officer wakes him with cold water, lets the Styx beat him with clubs, and has him interrogated even more. One day, the officer leads Chester to a room with the Old Styx. The Old Styx reads his Banishment sentence, much to the boy's horror. A few days later, Chester is blindfolded and marched through the Colony streets, which are filled with jeering Colonists. He is put on the Miners' Train, which starts its trek down to the Deeps.

Chester is a stocky 14-year-old boy with dark brown hair. He is known to have eczema, which flares up when he is in dirty/stressful situations. Not much else is known about what he looks like. He loves making BEKFAST.

Chester is in fact, a very sensitive person, despite being friends with the daredevil Will. Time and time again, has received the worst luck imaginable in comparison to other people in the series. This hardens him to the core, and he eventually becomes tougher and his sanity starts to slide.

However, he has a deep friendship with Will, which has been going on for years. He will try to defend his friend whenever possible. He also becomes good friends with Elliott and Drake. Later on, in Spiral, Stephanie tries to develop a romantic relationship with him. He enjoys this, much to Will's humor.

‘I had to come up with something quick. It wasn’t easy for me to say it, but I told her that she was my mother now my real mother was dead. And I also told her the only reason you and I were friends was because you reminded me so much of my sister. You know that she was knocked down and killed by some idiot in a stolen car when I was young?’ (to Stephanie, referring to a conversation he had with Martha. Terminal, page 122)

‘You said that your Brights can find anyone for you? I want him so badly. Can you really find him for me … find Danforth? Will you do that for me?’ (to Martha. Terminal, page 134)

‘No way! That creep is mine. And you bloody tell your Brights not to touch a bloody hair on his foul head. In fact, I want them to protect him … and keep him safe for me. He’s mine!’ (Terminal, page 170)

‘You’re next, Danforth!’

‘Keep out of it! Let me enjoy this moment. The moment I kill this stinking traitor.’ (to Stephanie)

But what? You weren't in the Hold. You didn't go through what I did. That little tramp was there when they were beating me! And she beat me, too. She was laughing like it was all some big joke. Well, I've got a punchline I'd really like to try on her!